Jim Reekes worked on iTunes from its inception. Now he says the app he used to consider the best in the world is “FUBAR.” And iTunes Radio isn’t helping.

IOS 7 is slated to hit devices today. There’s a new weather app and a new compass. Siri has an optional man voice. The new notification center might actually be worth using. Everything’s flatter, because iOS no longer has to coax people into the future with skeuomorphic odes to the past.

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iTunes has a new, whiter appearance, too–and Apple is introducing a new feature, iTunes Radio. Whether or not it’s a viable alternative for users of Spotify, Pandora, Rdio, or other streaming services, it’s still built on an app that’s gone off the rails, says Jim Reekes, an engineer and software designer who worked for Apple for more than a decade when iTunes was being developed. The problem, he says, is that iTunes has crept too far from it’s mission: “tunes.”

“I used to say iTunes was the best app of the decade. Now it’s gotten to be a pain in the ass,” Reekes says. “This app is trying to do way way too many things. It’s FUBAR.”

On one hand, Reekes says, the iTunes team pulled off an amazing feat–the iTunes Store has 500 million users in 119 countries who spent $2.4 billion on digital content in Q2 of this year alone. iTunes is one of the top revenue streams for Apple and it only seems to be growing. The business isn’t the problem. It’s the potential Apple’s missing to stay ahead of a growing batch of cheaper music services that offer streaming catalogs of music that can feel easier to access than iTunes. For many music lovers, iTunes is no longer the simplest way to experience music–even though simplicity has defined Apple’s most innovative, enduring designs. Just one example, Reekes says, is that it makes no sense in iTunes how “There’s a music (er, ‘media’) store that is only accessible by the iTunes app. Think about that: Why isn’t the iTunes Music Store just a normal website? It’s like if Amazon were only available on the Kindle, instead of all the desktop computers of the world.”

Far from an outside observer, Reekes, now senior principal consultant and trainer with the 280 Group, was there at the beginning of iTunes (in addition to his role developing key components in Macintosh). He came up with many of the ideas that remain key to the service today. His experience with what would become iTunes began in 1996, when he pitched execs at Apple on a music app that would download and organize MP3 files into playlists and then sync those with a simple portable MP3 player.

Bolting on so many non-music features into iTunes (tunes!) is turning the best app of the decade into a Frankenstein.

“I told them that people don’t want to ‘rip off’ music,” Reekes says. “They want to pay for it, but there’s no convenient way to purchase music on the Internet.”

He couldn’t get his managers on the QuickTime team interested. And neither the head of marketing for multimedia nor the VP for operating systems would bite. For Reekes it was, along with a few other mounting frustrations, the last straw. He quit Apple shortly thereafter to do a startup that incorporated a lot of his music and software ideas. It was called Kerbango Internet Radio. Kerbango built a database of about 6,000 web stations and broke them all down by attributes into categories. Users navigated Kerbango’s “tuning service” with a knob that had a press-to-select action. With it, they could scroll through a list of music types and stations and then press to select one or dig in to deeper folders. In other words, it’s was an early form of the click wheel.

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Meanwhile, Jeffrey Robbin, whom Reekes knew from his days at Apple, had co-created the SoundJam MP3 player. “He contacted me to help him with his software,” Reekes says.

SoundJam was bought by Apple and eventually morphed into iTunes (Robbin stayed on and still helps run it as Apple’s Vice President, Consumer Applications). Kerbango was sold to 3Com, which shuttered it. But Kerbango powered the Internet Radio component of the first edition of iTunes. “Jeff wanted to keep the tuning service, so Apple could provide radio stations in iTunes. Behind the scenes we gave him our code and the database,” Reekes says. The Kerbango tuning service is still mentioned as a key component in iTunes End User License Agreement (item 15 B. here).

Reekes contributed a few other big ideas that stuck, too: One was an idea for a smart folder that would automatically update based on musical tastes, a version of what would become the Genius folder in iTunes.

To be fair, iTunes is something much larger than the music-organization and distribution tool he and his colleagues envisioned. It’s a moneymaking monster that has dictated new terms for how music gets sold. But that’s precisely where the simple end-user focus got lost. “Bolting on so many non-music features into iTunes (tunes!) is turning the best app of the decade into a Frankenstein,” Reekes says. “I have no expectation that the ‘tunes’ part of iTunes will improve–ever.”

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About the author

Tyler Gray is the former Editorial Director of Fast Company and co-author of the book The Sonic Boom: How Sound Transforms the Way We Think, Feel and Buy (Houghton Mifflin Harcourt), out in fall 2014. He previously authored The Hit Charade for HarperCollins and has written for The New York Times, SPIN, Blender, Esquire, and others